Ichabod Crane is a man who was born in the 18th century, and was a former Oxford history professor who became a captain in the Revolutionary War. Being killed while in battle, Crane somehow awoke in a modern-day Sleepy Hollow. It was eventually revealed to him that his wife, Katrina Crane, and her coven had cast a spell on him in order to resurrect him and put him on the correct path as one of the witnesses mentioned in the biblical Book of Revelation. He found and formed a team with Abbie Mills, the second witness. As time went on, Crane learned that his son, whom was born after his battle with Death, is the Horseman of War.

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Crane was once a professor of history in Oxford, who was enlisted to fight in the British army. One of his early duties while in the British army was to capture Arthur Benard, a freed slave, suspected for treason. That's when Ichabod first met Arthur's nurse, Katrina, who was against his interrogation. Once alone, Arthur told Crane about demons who were disguised as soldiers and offered him a chance to fight alongside him. Afterward, the British lynched traitors in public as an example for the community. Ichabod opposed his colonel and thought executing people in public was wrong. His colonel accused him of being a traitor, which made Ichabod submit. However, within a brief second, he spotted his colonel's face change into something demonic. Katrina spoke of him being a true witness and a good man after this claim.

Arriving late to resume Arthur's interrogation, the colonel gave Ichabod the only option to redeem himself by taking Arthur to the forest and murdering him. Crane released him, and Arthur told him to repeat the words "Ordo Ab Chao" to Katrina and she shall bring him to George Washington. As Arthur escaped, he was murdered by the Colonel, who revealed himself to be a demon. After a unfair fight, it fled from the forest while Ichabod was taken back to Katrina for aid.[1]

Being enlisted in the Queen's Royal Regiment, he was sent to America to fight off soldiers. He grew weary of the tyranny in America through British rule and defected to the Continental Army, serving under General George Washington.[2]

In 1773, Ichabod was also a part of the Boston Tea Party movement (known at the time as 'The Destruction of the Tea'). It was a political movement that he claimed to invent. The natural intent of the movement was so that Ichabod, Samuel Adams, and the Virginia militia could stop a British shipment in order to retrieve a special weapon. The weapon, encased in a stone box, was guarded by a Hessian. The Hessian lit a bomb, sparing only Ichabod. Therefore, he took the box, and shipped it to Washington via ferry.[3]

Abraham rejects Ichabod's yielding.

One of the earliest events Crane has mentioned was his relationship with his former friend Abraham Van Brunt. Their relationship was very positive and the two did productive things with one another such as socializing at bars and practicing fencing. The two even left England together to join the American army. However, their friendship began to teeter once Abraham told him of Katrina, Abraham's betrothed. In 1774, Katrina confessed her love for Ichabod, which prompted her to leave Abraham. The next day, Ichabod and Abraham were tasked with an important duty to deliver the Declaration of Resolves of the First Continental Congress. Meanwhile, Icahbod admitted his knowledge of the break-up and Katrina's love for him. This flustered Abraham and the two began to duel in enemy territory. Abraham ended up getting shot by a red coat, and demanded Ichabod leave him to die.[4]

Before the war started, during a night of the blood moon, Ichabod's camp had been completely destroyed by overwhelming power, incomparable to average artillery. Tales told of Serilda of Abaddon. Washington claimed the redcoats foaming an alliance with the witch. Overtime, similar ambushes began to happen.[5]

In 1775, Crane guarded a safe house where Samuel Adams and John Hancock were avoiding arrest. Ichabod was on lookout and was alerted by a lantern, lit by Paul Revere, that the crown had arrived in American colonies. Just before he was going to tell Samuel Adams of the alert, he spotted Adam's giving a Paul a freemason manuscript that contained secrets.[6]

He even told Abbie that he had fought alongside with the Mohawk people, and utilized espionage. He mentioned that they were great spies and could go untraced.[7] He had also spoken in favor of abolishing slavery as he claimed he was part of the New York Abolitionist movement. During the war, he accepted an invitation to Lanchlan Fredricks' manor with Katrina. Fredrick's manor was basically a coven, and had many freed slaves that willingly worked at the residence.[8]

Crane rose through the ranks and during a discussion with Washington it was revealed that the Revolution was being fought not just for the freedom of the Thirteen Colonies, but also for the fate of all mankind. In 1781, Crane was also given a special task from Washington: to defeat a very specific Hessian soldier in battle, one who would be branded with the symbol of a bow on the back of his hand. When he faced the towering Redcoat in the field, Crane shot him, though his enemy arose nearly instantaneously. After being sliced in the chest by the enemy's broadaxe, Crane used his sword to decapitate the Redcoat. The two became linked by blood, and he seemingly died thereafter in triage, with his wife, Katrina, by his side, talking of a secret that he must know.[2]

Crane awoke in a cave in what he found to be 21st century Sleepy Hollow. Shocked and in awe by the strangeness of the time, Crane is indicted for the murder of police sheriff August Corbin, which was actually caused by the Headless Horseman. Crane plead for his case to the reluctant sheriff's deputy, Abbie Mills, who witnessed the murder herself. Crane is considered insane by the police and for the most part, Abbie, but she believed that Crane's knowledge could hold the key to solving the murder and finding the true killer. Abbie disobeyed orders and asked Crane to show her where he had awoken. Revisiting the cave, he came across a bible buried with him. The marked passage foretold the story of Revelation, which made Ichabod speculate that the Headless Horsemen is one of the four horsemen of the apocalypse.

The Headless Horseman struck again and Crane was dragged to a murder scene with Abbie, where he came across his wife's tombstone, stated "burnt for witchcraft". After a short argument, Abbie took Crane to a psychiatric ward and she revealed something supernatural that happened to her in the past. Once again Crane was visited by his wife, Katrina, who confirmed that she is a witch, given the duty of preventing the apocalypse. Katrina revealed that where her gravestone lays, is actually the horseman's skull, and that she is trapped in Purgatory. Katrina told Ichabod that he is the first witness, and must stop the Headless Horseman from retrieving his skull which would restore him to full power. Afterwards, Crane and Abbie, the second witness, successfully prevented the Horseman from getting his skull and formed an alliance.[2]

Staying the night in a motel, Ichabod was under surveillance by the police. He was visited by Katrina in a dream, forewarning him about an evil to come. Crane was then taken by Abbie to attend Corbin's funeral and he shared the pain with her by mourning his wife. However, that's when Crane came to the conclusion that the evil Katrina spoke of was a witch. After some time, they were called to a crime scene where the victim was burnt to ash, and oddly enough, Crane noticed his heart was missing. Searching for more information, Crane discovered and underground tunnel that led to a chamber where both could plan. Crane came to a conclusion that the witch hunts down her victims based on their bloodlines and who's ancestors killed her in the past. Crane and Abbie missed the chance of catching Serilda's after she obtained her target: a dead man's ashes. Using his ashes, she regained her flesh and pursued Ichabod. Using the gun power in the tunnels, he threw a torch to create a massive explosion, and defeated Serilda.[5]

The scorpion sting gives the dreamers full control in Ro'kenhronteys' world.

After witnessing a public suicide of a woman named Dr. Maura Vega. Abbie told Ichabod that Vega's eyes were white. When examining the eye, it exploded, being filled with sand. Abbie confessed to him that she had a nightmare that included Crane, a faceless creature and Dr. Vega, although she had never met her before. Crane and Abbie dug up files on Dr. Vega and found out that she was Jenny's former doctor. After a lot of convincing, Crane was taken to see Jenny. She agreed to speak with Ichabod alone, but he got nothing out of her because of her grudge with Abbie. Wanting to know more behind what damaged the sisters' relationship, Crane was told by Abbie that she didn't confess to seeing anything that day in the forest. Unlike Abbie, Jenny ended up in mental institutions.

Next visit was Garrett Gillespie, who found Abbie and Jenny when they were missing. It turned out Gillespie put himself at gunpoint and asked to speak with Abbie. After hearing gunshots, Ichabod ran to Abbie's aid, but Gillespie took his own life. After discussing Abbie's nightmare, Crane recalled connections to a creature named "Ro'kenhronteys" he heard of in the past. They both went to Seamus in hopes for defeating the creature. He prepared a ritual for Abbie, and Ichabod insisted that he'd join along to help Abbie face Ro'kenhronteys. With the help of Crane, Abbie destroyed Ro'kenhronteys. Afterward, Crane admitted to Abbie that it'd be best if she were to amend her relationship with Jenny.[7]

Patiently sitting in the car, Ichabod was approached by Abbie and notified that Jenny escaped from the institution. In the midst of receiving information, Ichabod was told of Abbie's difficult childhood. Ichabod suggested the best lead would be to visit Jenny's past foster homes to gain information on her whereabouts. Eventually, they learned of a cabin Jenny would go to in order to visit a friend. Breaking in the cabin, both recognized photographs with both Jenny and Corbin.

Eventually, they ran into Jenny who held them at gun point. Fed up by their senseless arguing, Ichabod silenced both sisters. Jenny immediately uncovered something that Corbin wanted to keep safe: A sextant. Ichabod helped understand the mechanism that was actually a projector that showed a map, created by Washington, of Sleepy Hollow from the 18th century. The map showed the location of a chest Ichabod found with his militia during The Boston Tea Party. Shortly, the group was ambushed by a modern-day Hessian group who escaped with the sextant. Holding one Hessian hostage, he killed himself with a cyanide pill after telling Crane their objectives; to use The Lesser Key of Solomon to unleash 76 demons upon Earth. His last words were "Moloch shall rise". Ichabod, Abbie and Crane reached the destination and stopped the Hessian group and destroyed the book. Ichabod himself learned that Moloch is the one who guarded Katrina in Purgatory.[3]

Crane is dragged on another emergency with Abbie, and is taken to a young, sick boy who spoke old English. Fluent in this language, Crane communicated with him and is told that he is from Roanoke. He and Abbie looked up cases on lost children and couldn't seem to find one on the young boy. Later, Ichabod was taken to the hospital where the young boy, listed as a John Doe, was a patient due to having an unidentified illness. The boy told Ichabod of an evil girl and Conquest. Ichabod came to the conclusion that he is from the sixteenth century Roanoke, also known as the lost colony.

Ichabod is quarantined after contracting the unidentified illness.

Using his skills to track down the village, Ichabod found the village with Abbie. Notably, all the villagers possessed the illness. Crane spoke with John Doe's father, and was told that the colony protected the people and prevented the illness from spreading. Upon returning back to Sleepy Hollow, Ichabod learned that the illness of John Doe began spreading like a plague and that Ichabod, himself, contracted it. While in quarantine, Ichabod awoke in Purgatory, and was found by Katrina. After speaking with her, he woke up being taken to Roanoke by Abbie. He was enlightened that the illness may go away once they are baptized in the colony's holy water. Ultimately, they were cured; John Doe, along with his village, and Conquest vanished.[9]

After enjoying a baseball game with Abbie, Ichabod departed from her to visit Katrina's grave. Strangely, Ichabod is shot with a tranquilizer dart. He gained back consciousness and awoke in an underground cell and was confronted by a man who was leader of the group, later identified as the Freemasons. Ichabod made it well know that he, too, is a mason. When requested, he told them stories of when he was a solider in the British army, and when he first learned of his place as a witness. When the Masons' learned of his connection to the Headless Horseman's, they came to a conclusion that Ichabod had to take his own life in order to end the horseman's in return. Afterward, he was found by Abbie, who highly refused to let him die and told him of the Sin Eater named Henry Parrish. Not wasting any time, Ichabod drank the poison he was given. After the poison began to take effect, he was approached by Henry, who quickly severed the link between Crane and horseman.[1]

Ichabod explained to Abbie that the Freemasons planned to have a meeting to discuss a way to defeat the Headless Horseman. Abbie, on the other hand, wasn't allowed to attend the meeting, but Ichabod eventually insisted. Later that night, Ichabod reached the masonic lodge and was alerted by gunshots inside the residence. Armed with a sword, Ichabod investigated and witnessed the Masons decapitated. Running into Abbie, they spotted the Headless Horseman fleeing the scene. While the police department investigated the crime scene, Ichabod searched for clues to defeat the horseman, and he realized that the horseman was looking for his skull. With the permission of Captain Irving, Ichabod came to a conclusion that they had to destroy it. After multiple attempts, the skull couldn't be destroyed.

Finally, Ichabod and Abbie found the heads of the Mason's which were hanging from a building like lanterns. Ichabod told Abbie stories of the use of lanterns in his past, and mentioned remembering a manuscript that told of secrets to destroy the horseman. The next day, Ichabod and Abbie visited the Tarrytown Museum of Colonial History to locate the manuscript. Meanwhile being taken away from interrupting a tour, Abbie notified Ichabod that the manuscript was accessible online. While alone, Ichabod deciphered the manuscript by revealing a hidden password engraved in the back of the skull's teeth. He found Abbie, holding Andy at gunpoint. After Andy left, she told Ichabod that Andy shared information that the horseman could be caught. With the help of Frank, they created a diversion and lured the horseman into the masonic cell, weakening him with ultraviolet lights.[6]

Crane is very much a duty-driven man, except when it comes to his wife. Ichabod's love for his wife is a driving force in his motovation. Crane is also very loyal to his friends, and values honor of all. He also loves his son and, despite him becoming War, will never lose hope in him.

and Katrina placed Jeremy in the care of Grace Dixon and her husband, leaving him with a makeshift doll that would serve as his protector in the absence of his parents. Jeremy's cry initiated a fire, which killed both Grace and her husband, and he was soon after placed in an orphanage.

Ichabod first met Katrina when she was a Quaker friend of a man named Arthur Bernard. Ichabod, who worked as a Redcoat at the time, was sent to interrogate and even kill. Katrina was bitter and cold to Ichabod, despite his attempt to be charming. Katrina, however, could look at him and tell of the good man for whom he truly is. When he implied seeing something evil in one of the Hessians, she warned him of the dangers he was in. When Ichabod was sent with Arthur Bernard out into the woods to be shot, but when Ichabod set him free, his commanding officer shot Arthur and revealed himself to be a demon. Ichabod fought him, but ended up wounded. Katrina saw him outside her window and helped him inside to treat him. Since then, he made a pledge to fight against evil.[1] He and Katrina became well acquainted since then.

Much to Ichabod's concern, Katrina was betrothed to Ichabod's best friend, Abraham Van Brunt. While shopping for a necklace for Katrina, Abraham asked for Ichabod's advice and he ended up choosing a necklace the perfectly suited her. At a party, she confessed her love for Ichabod, and told him she was going to break off the engagement. Ichabod wasn't fond of the idea. Not long after, she did. While on a mission through enemy territory, Ichabod confessed, saying he knew, and that he and Katrina would like his blessing. Abraham acted out in anger, and soon died from the Redcoats, resulting in becoming the Horseman of Death.[4]

When proposing to Katrina, Ichabod hadn't mentioned his former fiance named Mary Wells. It was until Mary Wells showed up to continue their relationship, that Ichabod told Mary the truth.[10]

Though Katrina and Ichabod were married not long after Ichabod became a Patriot and fought for General Washington, Ichabod had no idea Katrina was a witch. Only after his death and resurrection did he find out she cast a spell on him. When with Abbie Mills Ichabod found Katrina's gravestone, she had been burnt for witchcraft.[2] Since then, Katrina has only been able to contact Ichabod through dreams and visions, finding out that she was trapped in Purgatory. Ichabod has displayed signs of anguish in regards to the whereabouts of his wife. During Corbin's funeral, Ichabod, too, mourned his wife's absence.[5] The thought of even celebrating Thanksgiving without her bothered him as well.[8]

It was also revealed that Katrina left for a short time to give birth to their only son Jeremy Crane. However, a danger in the house she birthed in forced her to leave. She didn't tell Ichabod about their baby, which began to fracture their relationship as husband and wife.[8]

With the help of a man named Henry Parish, he helped Ichabod enter Purgatory. Regardless of her warnings to not do so, Ichabod came to her rescue. In order for Katrina to leave Purgatory, a soul would need to take her place. Abbie sacrificed her soul to stay behind, and Ichabod was grateful, promising to return and save her. Being united with Katrina, it didn't take much time before Katrina was held captive, by Henry, again.[11]

After victoriously capturing Abraham, Abbie teaches Ichabod the fist bump as a result of their teamwork.

Being the second witness, Ichabod's partnership with Abbie has transformed into loyalty since they first met. When Ichabod first met Abbie, it took her a while to warm up to him. Confused by the era he was in, he assumed Abbie was an emancipated slave, but he assured to her that he wasn't a racist and was apart of the abolitionist movement. Crane never understood how Abbie could be such a skeptic, but eventually learned the truths of her past as a teenager. This made Ichabod sympathetic to Abbie, which made her the same in return. After being ordered to be taken to a mental institution, Crane was removed by Abbie and have been working together ever since.[2] He excessively calls her "lieutenant" and rarely by her first or surname.

It didn't take long for Crane to gain Abbie's trust and vise-versa. Ichabod realized that he could tell Abbie things that were bothering him if he sought comfort. They both, for instance, share a sarcastic wit they commonly use to lighten the mood in their everyday life or in the most inappropriate moments. Crane first put his very own line on the line for Abbie confronting Ro'kenhronteys. Ichabod drank the a substance that would send him to Ro'kenhronteys' world so that Abbie wouldn't have to face him alone.[7]

When Ichabod first entered Purgatory with Abbie to save Katrina, Katrina couldn't leave without a soul taking her place. Abbie insisted, but Ichabod strongly opposed. Abbie convinced Ichabod to trust her, and before separating, promised that he would return for her.[11] Doing everything in his power and knowledge, he obtained a key that could loophole two souls out of Purgatory at once. Ichabod kept his promise and freed Abbie from Purgatory.[12]

Later, he displayed signs of being protective. When Ichabod learned that Nicholas Hawley had feelings for her, he indirectly discussed with Abbie that it wouldn't be wise to get into a relationship with such a man who only cared about profit.[13] Another time was when he lured away Abraham, getting shot at, to prevent him from discovering where Abbie was hidden.[14] Again, Abbie had gotten shot in the shoulder, terrified and angered, Crane vengefully killed the demon. Crane has ultimately come to an understanding that Abbie's life and well-being matters to him and that he can't fulfill this path without her.[15]